Just when things were looking lively for Miranda, her new date Will fails to show up for three hours. Determined to fight back against the injustice of this "illegal dumping," she calls Will's home number and finds out that he is never going to show up -- he died last night. Stunned, Miranda agrees to pay her respects at the wake where she finds a very cute, but very dead Will. But all hope is not lost. At the wake, Miranda hits it off with Jim, one of Carrie's ex-boyfriends from years past. Carrie warns her that he's a jerk, but Miranda agrees to meet him for a date anyway, only to find out for herself that he really is a jerk. Carrie teaches a seminar about meeting men to a packed crowd of incredibly cynical and frustrated New York women. After a few pointed questions from the audience ("Have you ever been married?"), the class realizes Carrie may have written a lot about men and relationships, but she's still as clueless as the rest of them. Charlotte and Trey work on bringing "Schooner" and "Rebecca" into the harbor, but the wind never gets going. Over brunch the next morning, Charlotte tells the girls about her problems, and Samantha dishes out some raw sex advice which Charlotte finds offensive, but secretly useful. Meanwhile, while shopping for pashmina, Samantha finds her sexy, feisty clone, Claire Anne. They go out for a drink and meet two cute guys, but Claire Anne takes the sexual forwardness too far even for Samantha when she crawls under the table to get busy with one of the men. Meanwhile, on Samantha's advice, Charlotte makes herself more sexy for Trey by wearing revealing lingerie and touching herself -- it works! And for her second class, Carrie finds most of her students have dropped out. Instead of lecturing them, she decides to hit the bars and give them some real experience in the field.

Samantha and Carrie are having trouble getting their beauty sleep. Samantha is bothered by the late-night cackling and ranting of the transsexual prostitutes outside her window, while Carrie is awakened a tad too early by roosters crowing on a nearby rooftop. Carrie and Miranda spot Steve and Aidan and their dogs at an outdoor cafe. They decide they can't avoid interaction and approach their exes, only to discover they have new girlfriends. Carrie wonders if maybe everything isn't the man's fault, if maybe the problem is them. Carrie gets an even bigger wake-up call when Big rings her up and asks her to lunch at the Boathouse in Central Park. Carrie agrees to go and when she confides in Miranda, the friends have their first big fight. Miranda tells Carrie that it's a huge mistake to see Big again and Carrie calls Miranda "judgmental." Miranda, who feels like she's in a life rut, runs into Steve at her local Chinese restaurant. They have a nice friendly exchange, and Steve allays some of Miranda's fears. Meanwhile, Charlotte, in her new-old single-girl apartment gets a 4am visit from Trey, who turns on the heat and manages to keep his Schooner going with Rebecca. After their sexy session, the couple has a real heart-to-heart about their marriage, but no decisions are made. Carrie calls Miranda before she meets Big and the girls make up. At the Boathouse, Carrie and Big fall into the pond and go back to Big's place to dry off. Carrie says the two are like "war buddies." Big hints that Carrie can stay a while, but Carrie says "It's a good idea in theory, but somehow it doesn't quite work." She leaves. After some serious cat-fighting with the transsexuals, Samantha ends up inviting them, plus Carrie, Miranda, and Samantha, over for a roof party. The girls all get down, drink Flirtinis and try to stop obsessing.